Stigmastanol

Base Information

• Chemical Name: Stigmastanol
• CAS No.: 83-45-4
• Molecular Formula: C29H52 O
• Molecular Weight: 416.731
• European Community (EC) Number: 201-479-0
• NSC Number: 49081
• UNII: C2NJ9WO6O7
• DSSTox Substance ID: DTXSID201016169
• Nikkaji Number: J4.631K
• Wikipedia: Stigmastanol
• Wikidata: Q3973521
• NCI Thesaurus Code: C68323
• Metabolomics Workbench ID: 34946
• ChEMBL ID: CHEMBL252364
• Mol file: 83-45-4.mol

Synonyms:24 alpha-ethyl-5 alpha-cholestan-3 beta-ol;24 alpha-ethyl-5 beta-cholestan-3 alpha-ol;beta-sitostanol;dihydrositosterol;sitostanol;stigmastanol;stigmastanol, (3beta,5beta,24S)-isomer

Chemical Property of Stigmastanol

Chemical Property:

• Melting Point: 144°C
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 474.98°C (rough estimate)
• PKA: 15.14±0.70(Predicted)
• Flash Point: 197.1oC
• PSA: 20.23000
• Density: 0.9444 (rough estimate)
• LogP: 8.10470
• XLogP3: 10.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 416.401816278
• Heavy Atom Count: 30
• Complexity: 583

Purity/Quality:

98% ^*data from raw suppliers

Stigmastanol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)C(C)C
• Isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
• Uses: Stigmastanol is used in food product formulations for prevention and treatment of hypercholesterolemia, hypertension and inflammation disorders in humans

Technology Process of Stigmastanol

There total 50 articles about Stigmastanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

β-sitosterol (83-46-5) → Stigmastanol (83-45-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 24h; Inert atmosphere;

DOI:10.1007/s12272-012-0308-3

Reference yield: 82.0%

Stigmasterol (83-48-7) → Stigmastanol (83-45-4)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In dichloromethane; for 6h; Irradiation;

DOI:10.1016/S0039-128X(97)00010-X

Reference yield: 76.0%

Stigmasterol (83-48-7) → β-sitosterol (83-46-5) + Stigmastanol (83-45-4)

Guidance literature:

With hydrogen; Raney-Nickel W₂; In ethyl acetate; at 20 ℃; for 15h; Further Variations:; molar ratios; Product distribution; atmospheric pressure;

DOI:10.1016/j.steroids.2008.02.004

upstream raw materials:

β-sitosterol

stigmast-5-en-3-yl acetate

Fucosterol

3β-acetoxy-5α-stigmastene-(14)

Downstream raw materials:

stigmastan-3-one

3-O-(trans-4-O-acetylferuloyl)-β-sitostanol

cis-androsterone

androsterone acetate

Refernces

• 1、 Anderson,Shriner,Burr. "-". . p. 2987,2994. Retrieved 1926.
• 2、 Lee, Sujin,Marharjan, Sony,Jung, Jong-Wha,Kim, Nam-Jung,Kim, Kyeojin,Han, Young Taek,Lim, Changjin,Choi, Hyun-Jung,Kwon, Young-Geun,Suh, Young-Ger. "Novel human umbilical vein endothelial cells (HUVEC)-apoptosis inhibitory phytosterol analogues: Insight into their structure-activity relationships". experimental part. p. 455 - 460. Retrieved 2012/08/28.
• 3、 Geoffroy, Philippe,Julien-David, Diane,Marchioni, Eric,Raul, Francis,Aoude-Werner, Dalal,Miesch, Michel. "Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols". . p. 702 - 707. Retrieved 2008/09/21.